Cyclo(Phe-Leu)

Base Information

• Chemical Name: Cyclo(Phe-Leu)
• CAS No.: 3354-31-2
• Molecular Formula: C15H20N2O2
• Molecular Weight: 260.336
• Mol file: 3354-31-2.mol

Synonyms:(S)-3-Benzyl-6-isobutyl-piperazine-2,5-dione;c-L-Leu-D-Phe;3-benzyl-6-isobutyl-piperazine-2,5-dione;3-Benzyl-6-isobutyl-2.5-dioxo-piperazin, Leucyl-phenylalanin-anhydrid;Cyclo-leu-phe;3-Benzyl-6-isobutyl-piperazin-2,5-dion;3-Benzyl-6-isobutylpiperazine-2,5-dione;

Chemical Property of Cyclo(Phe-Leu)

Chemical Property:

• Melting Point: 265 - 267 °C
• PSA: 58.20000
• LogP: 1.91600

Purity/Quality:

99% ^*data from raw suppliers

Cyclo(Phe-Leu) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclo(Phe-Leu)

There total 27 articles about Cyclo(Phe-Leu) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Leu-Phe-OH (3063-05-6) → (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione (3354-31-2,4156-30-3,7280-77-5,16679-70-2,16679-71-3)

Guidance literature:

With (3-{[(cyclohexylimino)methylidene]amino}propyl)oxy linked polystyrene resin; In dichloromethane; N,N-dimethyl-formamide; for 0.0833333h; Flow reactor;

DOI:10.1021/acscombsci.0c00001

Reference yield: 95.0%

(S)-Leu-OMe (2666-93-5) + N-Fmoc L-Phe (35661-40-6) → (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione (3354-31-2,4156-30-3,7280-77-5,16679-70-2,16679-71-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/j.tetlet.2021.152895

Reference yield: 90.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione (3354-31-2,4156-30-3,7280-77-5,16679-70-2,16679-71-3)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

With trifluoroacetic acid; In dichloromethane; for 0.5h;

N-tert-butoxycarbonyl-L-phenylalanine; Further stages;

DOI:10.1016/j.tet.2015.08.051

upstream raw materials:

(D,L)-Phenylalanyl-(D,L)-leucine

N-tert-butoxycarbonyl-L-leucine

Boc-L-Leu-D-Phe-OMe

D-phenylalanine methyl ester hydrochloride

Refernces

• 1、 Aldrich-Wright, Janice R.,Dankers, Christian,Gordon, Christopher P.,Harman, David G.,Nguyen, Thanh V.,Tadros, Joseph. "Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization". supporting information. p. 255 - 267. Retrieved 2020/06/05.
• 2、 Bérubé, Christopher,Barbeau, Xavier,Cardinal, Sébastien,Boudreault, Pierre-Luc,Bouchard, Corinne,Delcey, Nicolas,Lagüe, Patrick,Voyer, Normand. "Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides". . p. 330 - 349. Retrieved 2017/03/15.